Daniel Mallory Ortberg is online weekly to chat live with readers. Here’s an edited transcript of this week’s chat.

Q. Boyfriend will not apologize: My boyfriend feels like he only needs to apologize when he thinks what he did was wrong, and that’s never. The problem seems to be twofold. First, he sees the world in two ways: people who think like him, and people who are wrong. If something would not upset him, then it should not upset me—end of story. This extends to every aspect of his life: There’s only one way to make a sandwich or to put away groceries, and that’s his, and if I don’t do it his way, he stands over me and criticizes me—he says he’s helping me do it correctly—and then wonders why he’s left doing all the chores. Second, he bean-counts and is in constant competition in our relationship to be the least wrong.

The worst part is I cannot have a discussion with him about this. No matter how calm I come at it, he immediately refuses to discuss the matter and says, “Everything I do is wrong, and you are perfect.” I even went so far as to record all the times I am wrong and apologize to him, which was about once a day. He has apologized once in two years, and it was not willingly. He has very low self-esteem and a hypercritical mother, but I’m at my wits’ end here! Help.

A: Leave him! When you find yourself saying things like “The reason my boyfriend never apologizes is because it’s his mother’s fault, and also he doesn’t have high enough self-esteem,” you have reached Critical Dumping Him Mass. He is a grown man, and while many of us are plagued by mother issues, they don’t make it impossible for anyone to offer an apology when they’re in the wrong. Worse, the implication of “he has low self-esteem” is that it’s your job to build his self-esteem up sufficiently that he’ll be able to have a disagreement with you about fridge arrangements without needing to stake out and die upon the One True Fridge-Arranging Hill. Which means that not only will you never get the apology you’re longing for, or an admission that you might both have good points, it’ll also be your fault that he doesn’t apologize because you haven’t sufficiently improved his self-esteem. What an ouroboros of garbage! You have even taken to keeping a notebook of your own apologies because you’re starting to feel like there’s something wrong with your version of reality. Surely this is not what you envisioned when you started dating this guy—“Man, I can’t wait to get a journal where I track all of the times I apologize to keep him happy and in order to remind myself that I’m not making up the one-sided nature of our arguments.” Leave, don’t try to fix him, and be happy.

Q. Grandma’s quilt: Before she died, my mother made wedding quilts for all of her grandchildren. I’ve been left in charge of them and decided to hand them over to each grandchild’s parent. The quilt made for my youngest brother’s child still needs a label, which presents me with a dilemma. His child is transgender, but my mother never accepted this fact. I want to honor both of them and have kicked around the idea of writing, “For my beloved grandchild. Love, [mom’s name].” But I wonder if this really honors my nephew, as it’s so generic. A huge part of me wants to include his name, a name my mother refused to use. I love my nephew and completely accept him. I want this quilt to be a loving gesture, not a reminder that grandma’s love seemed contingent upon his gender identity.

A: I think that’s a lovely idea. My guess is that your nephew will know the addition came from you and that his grandmother did not in fact come to terms with his transition before she died. But that won’t make the label any less special.

There are lots of cases in which I think gender-neutral language is an improvement on unnecessarily gendered language, but this isn’t one of them. Politely saying “child” or “person” when you know someone has transitioned to a specific, hard-fought identity can feel impersonal and like you’re holding them at arm’s length, which isn’t the message you want to communicate at all. I don’t think you’re required to honor your mother’s refusal to use your nephew’s name. She made the quilt, and you’re discharging your duty to her memory by passing it along, but you’re the one writing the label. Use his name.

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Q. Stumbling out of the closet: My two closest friends, “Mark” and “Megan,” have been dating for a couple of years. I was already close with both before they started seeing each other, and now both have separately spoken to me about difficulties in their relationship. Each of them knows that the other has spoken to me but have respected the separate friendships enough to not ask what the other has said. The problem is this: Mark has stopped speaking to Megan without saying why, and it’s causing her tremendous fear and uncertainty. Meanwhile, I know why, but only because Mark told me while drunk. He’s gay and wants to break up so he can pursue a relationship with a man, but he’s been afraid of hurting Megan—and also of coming out, which I think makes up more of his fear than he admits or realizes.

I told him he has to just tear off the Band-Aid. He seemed to accept that at the time, but he was drunk, so I’m worried he’s going to back out in the light of day. It’s obviously wrong to out someone against their will, but surely there’s a point where my obligation to protect Mark’s privacy ends and my duty to be honest with Megan begins. How long should I give him to do the right thing before I do it for him? Or do I just have to sit on the sidelines indefinitely?

A: At a certain point, I think Megan will take the fact that her boyfriend has completely stopped speaking to her as a breakup, so the basic problem will take care of itself. But I agree that you have reason to revisit the conversation with Mark. Tell him that even if he’s not ready to out himself to her, he owes her at least a conversation about the fact that he’s ending their relationship—now. And if he plans on dating guys next, she’s probably going to figure things out sooner rather than later. You don’t have to be too hard on him during this conversation, but certainly encourage him to see that telling her is probably an inevitability, and she’d probably rather know the truth than wonder in agony about what she did wrong.

Q. Family visits: I just came back from visiting my family for the holidays. Every time I visit, I disappoint my brother. My brother and sister-in-law are members of an organization that has a bar. They spend a great deal of time there and always want me to go with them. I rarely drink. For medical reasons, alcohol affects me quickly, so I don’t drink and drive. I’m very uncomfortable in bars. I know my brother wants me to meet his friends, so he is disappointed I won’t go. When I am there and the two of them go to the club for “just one or two drinks,” they get plastered. I’ve thought of going for just one drink (a Coke) and driving separately, but that isn’t going to satisfy my brother. He really wants me to drink. How do I appease him?

A: Don’t appease him. Your brother is being an asshole. He knows you rarely drink, that drinking affects you quickly and in a way you don’t like, that you don’t enjoy being in bars, and yet he repeatedly insists on dragging you to bars and watching him get wasted. You’ve already spent a lot of time and energy trying to appease him, and that still hasn’t made him happy. The answer isn’t try to appease him more. My guess is that anything short of drinking exactly like your brother is going to disappoint him, because he cares more about lending an air of legitimacy and normality to his binge drinking than he does about your comfort and happiness. Let him try to meet you halfway, for once. If he isn’t willing to socialize at a restaurant or a coffee shop or a movie theater or someplace that doesn’t revolve around drinking, make plans elsewhere that don’t involve him.

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Q. My mother talks too much and turns people off: My mother is in her 70s, and most people find her charming, sweet, and attractive. She is single (twice divorced), still looking for love, and can’t seem to meet anyone. I think this is because Mom talks nonstop. When I am with her, she can do a monologue for an hour with no encouragement from me other than an occasional “hmmmm.” If I ask her a question, she has to explain herself with anecdotes and diversions into other topics. She repeats many of the same stories. Everything needs to be thoroughly explained. She claims any man who is interested in her always loses interest. She can’t get a second date. She blames her age and looks, but many people tell me how beautiful she is and how great she looks for her age. I think it’s because men can’t stand her constant talking. I am willing to indulge her because she’s my mother, but I can’t imagine how a total stranger would want to spend any long period of time with her, let alone have a serious relationship.

I don’t know how to say this to her without hurting her feelings. I tried to tell her once how much she talks, but she uses the excuse that she’s lonely and has nobody to talk to. She is an active senior with many hobbies who belongs to various clubs and does volunteer work. She does have people to talk to when she leaves the house. Unfortunately, if one person gives her their undivided attention, she just can’t seem to help herself. She is a retired psychologist, so she does have listening skills. How can I tell her to start using them?

A: I can appreciate that you love your mother and want to help her, but I think if she’s in her 70s and has already been married twice, this is a problem she’ll have to handle on her own without assistance from her children. You’ve already suggested that her conversational skills may be a factor, and she disagrees. Pushing further would unnecessarily entangle you in her dating life.

Instead, think about whether you’re actually as fine with only listening when she’s talking to you as you claim to be. I think you have real grounds for saying, “Mom, I love talking to you, but when we talk, you often monologue for an hour and don’t give me a chance to reflect or ask questions or tell you what I’m up to. Are you willing to try something a little different the next time we talk? It would mean a lot to me.” Don’t try to offload your own discomfort at something that does affect you—your relationship with your mother—onto something that doesn’t—whether she gets a second date with a stranger.

Q. Burned out: The last five years have been hellish for me: I raised my grandson while my daughter worked, struggled to finish grad school, and got a divorce. My husband died. I watched my daughter get remarried. I gave them the house my husband and I paid off. It hurts too much to spend any more time in there. I feel empty, hollow, and unhappy. My sisters have moved back to our home country with their husbands. I was born here, but other than my daughter and grandson, all my living family are there. My family tells me I am welcome and missed. I have decided to move back. When I told my daughter this, she grew incredibly upset with me. She and her husband are planning to have more children and assumed I would stay and raise them like I did my grandson. I told her that I was homesick and wanted to go see my family again. The last time I saw my sisters was when my husband died. She accused me of “abandoning” my real family, meaning her and my grandson. If she had struck me, it would have hurt less. My daughter refuses to speak more on the subject and will not apologize to me. Our conversations revolve around my grandson. She hasn’t even told her husband about my plans. I don’t know what to do. I do not know how to deal with my daughter. Please assist me.

A: I’m so sorry your daughter is adding unnecessary stress and pain to this move. I’m extremely glad to hear that you’re going ahead with it anyway, and I hope you find that being with the rest of your family is peaceful, energizing, and soothing. It’s a shame that your daughter made an assumption about what you were going to do with the rest of your life without consulting you. She has created a problem that did not need to exist, all on her own. I realize that she’s your daughter and that you’ve had a habit of helping her out, so it may feel daunting to contemplate moving away without making sure she and her husband understand your decision, are happy about it, and have alternative child care plans set up first. But it’s worth doing so for your own peace of mind, I think. You should take a break from these conversations with your daughter if you need one. Don’t let her guilt you into believing you’ve misled or hurt her. She has a partner and a paid-off house. The two of them need to figure out a family plan that’s not just assume Mom will happily raise our kids for us because she helped us out in the past. You can tell her that she’s hurt you, that you love her and will be happy to hear her apology whenever she’s ready, but that you’re moving away and it’s not up for debate. Then focus on planning your move and seeing the rest of your family. Good luck.

Q. I just want to contribute: I’m an older woman who has been single for almost 20 years. I met a younger gentleman in late summer. Because it had been so long, friends had to point out to me that I was being wooed. I thought he just liked to hang out as we have quite a few mutual interests. Since that realization, our relationship has deepened, and we’ve acknowledged that we are in an early stage of love. My daughter, from my previous marriage, has given her approval. My cats even like him. I couldn’t be happier.

So what’s the issue? He has way more money than I do. He pays for everything. My ex was emotionally distant, so my daughter and I agreed I’ve probably been “on my own” going on 30 years. I did everything because he wouldn’t. I have a 40-hour-a-week job I enjoy, and, having been on my own for so long, I’ve learned how to budget and save for things. But my budget only stretches so far. My boyfriend paid to get my back door fixed after I mentioned I’d saved to do that. He pays for groceries when we stay at each other’s homes. He’s got two houses and has flown me to each for extended weekends together, even paying the catsitter. I’ll often find money in my purse after time together. “For expenses,” he says.

It sounds great, I know, but when my boyfriend picks up the tab for everything, I feel like a gold digger. We talk about everything, and I’ve explained that I want to pick up the tab for an inexpensive night out or buy the groceries when he comes to visit, but he won’t hear of it. The last time he visited, I bought the groceries before he came. He stuck money for them in my coat pocket where he knew I wouldn’t find it until Monday, after he’d left. He says he understands my need to feel like I’m contributing monetarily to our relationship, but he has also said that he wants to indulge me because I’m the first woman he’s ever felt a deep connection to. I’ve had to watch what I say because he will, if I admire something in a store, buy it for me. I don’t need stuff, I’ve told him. I just need him. We have not argued, as such, over this point, but I’m not sure what I can say to get him to understand that I want to contribute on occasion, as I am able, because it makes me feel good. We vowed not to keep secrets from each other, but I’m finding myself not being honest about my finances because I don’t want him paying for everything. Any suggestions?

A: I think splitting grocery costs or paying for you to visit him is lovely and generous, but sneaking money into your purse and refusing to let you buy him a slice of pizza once in a while is neither. Since it hasn’t yet become a point of serious contention between you, I’m hopeful that he’s just a little clueless and not actually dismissive of your feelings. Let him know where you need to draw the line. “You need to stop putting money in my purse and coat. If you do it again, I’m going to give the money back. I enjoy and appreciate your generosity, but when you sneak money into my stuff despite knowing I don’t want it, I don’t feel valued or listened to. You want to indulge me—great. If you indulge me in ways I’ve told you I don’t want, that tells me you want to feel indulgent and like a big shot more than you actually want me to get what I want. It’s not just a cute little whim that I want to occasionally buy us an inexpensive meal. It’s important to me, and if you care about me, you’ll respect that.”

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Q. Stuck in between: I’m a trans woman who generally “passes” in my life: I only get misgendered occasionally and am only asked about my transness a couple times a year. There have only been two bad instances with this. Once, when I was trying to use the restroom, a guy grabbed me and wouldn’t let me use the bathroom. The other time, when I was raped, the officer spent an exorbitant amount of time trying to ascertain my gender. Now that I’m married, I have thankfully stopped getting intrusive questions about whether I’m “pre- or post-op” from men at bars and on dates, although when we’re out with our son we do get asked if we adopted or had a surrogate.

The thing is, I’m not exactly a trans woman. I was assigned female at birth but have a hormonal condition. I participate in some groups with trans people. These groups help me because I can relate to a lot of their feelings and experiences. When I try to talk to my cis friends and family, they just tell me I’m beautiful and loved for who I am, which isn’t the point. But occasionally the group members talk about experiences they’ve had that I don’t share. Part of me feels like I shouldn’t join in because I wasn’t assigned male at birth, and while I can relate in a lot of ways, it’s still not the same experience. These things are really painful, and I would hate to make other people feel like they can’t talk about them with their community because some cis person is going to chime in. I realize that if I did ever say anything about my birth assignment, I might be told I’m intruding or that I’m just not wanted, which I’m prepared to hear and respect. Do you think I should try to ask about my participation, or is it better to just let them have their space?

A: I don’t have any sort of authority to tell you that all trans women in these groups will have the same response to your presence. If any of these groups are online, that makes things a little easier, because it’s not as if there’s limited physical space or time for an in-person meeting. If any of these groups are in-person, I think it’s slightly more important to check in with your fellow members. I think your intentions are good and your shared experiences are material and extensive. Again, that’s not a guarantee that all trans people will think the same thing, but I do think it’s a useful foundation to build on. If any of these groups have moderators, you might consider asking them if they consider their group’s target audience to include you. You might also look to see if, in addition to these groups, there are others serving women with your particular hormonal condition. I think that if you’re prepared to respect “no” if you hear it, and that if you’re generally looking for support in dealing with misgendering, intrusive questions about your body, and dealing with cis people who have a hard time understanding your experience, you deserve a place to talk about it. I hope you find solidarity, support, and companionship.

Q. Re: Burned out: The letter writer says her daughter expects her to “raise” future grandkids. There is a huge difference between raising someone else’s child and providing child care while a parent works. Would you say a nanny is “raising” a working mom’s child? Isn’t it possible the daughter only expects the letter writer to provide child care?

A: I think it’s a fairly minor distinction. While there may be a difference between “change your plans about moving home so you can help out with child care most days of the week” and “change your plans so you can provide child care every day of the week,” both requests are unreasonable.

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Q. My mother-in-law hopes we die: My husband, our three young children, and I recently went on a vacation with my in-laws. We provided the accommodations. My mother-in-law tries to act more like our children’s mother than a grandmother. She loves her grandchildren, but she is very interfering, judgmental, and disrespectful to me and my husband. On this recent visit she brought a children’s book for our 5-year-old daughter that was missing the last two pages. The book was about a girl who visits her grandmother for the summer every year; my MIL wrote an ending with my daughter that said the girl’s parents died and she got to live with her grandmother forever. It was written like a happy ending! When we confronted her (away from the children) that it was inappropriate, she blamed our 5-year-old saying it was all her idea. I am so upset I can’t even look at this woman; and now she is suggesting we get together again next month to go camping. What should we do?

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